Benzaldehyde → 2-Propenoic acid, 3-phenyl-

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=C=O.[C:12]([O-:15])(=[O:14])[CH3:13].[K+]>>[C:12]([OH:15])(=[O:14])[CH:13]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 10038Ketene

HCID 517044Potassium Acetate

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 22%

Procedure

It is also known that benzaldehyde and ketene can be reacted in the presence of potassium acetate to give a primary product from which about 22% of cinnamic acid is obtained (J.Am.Chem.Soc. 55, 275 (1933)). Under similar conditions, 30% of cinnamic acid and 70% of styrene were also obtained (Organic Synthesis, Volume I, 215 and 216 C. D. Hurd. C. L. Thomas, (1942)).

Sources & evidence

ORD record: ord-527ebacae13141b9b6a3a23586ffcc09
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04609756

Reaction notes

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